He made his name as a technology entrepreneur, then shifted to venture capital, and now Raj Singh’s career is again in a state of flux. Most people know Singh for the simple fact that startups Cerent, Siara and StratumOne — all of which he played a part in founding — were acquired for a staggering combined $11 billion in 1999. He was a veritable money-making machine for Vinod Khosla at VC firm Kleiner Perkins during the tech boom. So Singh shifted gears and became a VC himself, co-founding Redwood Venture Partners and Comstellar Technologies. “It has more to do with my personality, I like to do new things,” he says. But this time the change of scene is more drastic — Singh has launched himself into a new arena: the movie industry. And we’re not talking about building or funding networking gear to enable digital film technologies. Singh is passionately pursuing the life of the independent film producer — and he even hopes to sit in the director’s chair some time soon.

“It was not a planned change,” he explains, while making it clear that he still splits his time 50-50 between his duties as a general partner at Redwood and his cinematic endeavors. “I met a couple of people who had graduated from UCLA and USC in film making. They were venturing out into the film business. I met them and got impressed with their background and what they wanted to do. So I decided to work with them.”

Together with Digvijay Singh and Mayank Chhaya, Singh founded Literate World, which is a publishing, media and cinema startup based in Fremont, CA. The idea behind the new company is to showcase new talent — publishing international books, producing TV programming and producing films through Kundalini Pictures, which is the new company’s cinema production arm.

Mr. Executive Producer

It is with director Digvijay Singh’s debut film “Maya” — produced by Kundalini Pictures — that Singh has made his first foray into the film industry. And it’s not a shabby start. Singh executive produced the film, which is in Hindi, and deals with child abuse. It was entered into a number of film festivals across the world and achieved considerable recognition — notably at the Toronto Film Festival, where it was first runner up behind “Amélie” and ahead of second runner up “Monsoon Wedding.” Singh seems to have enjoyed his experience with film festivals (he event took Maya to the celebrated Cannes Film Festival, where the film played in the circuit to court distributors but wasn’t entered in the competition).

“The high-tech industry is so much obsessed with progress, and money and competition. Whereas in the independent film industry you meet people with artistic minds, and they appreciate other people’s work,” says Singh. And he seems intent on entering fully into the world of cinema.

His second project came about when he met USC film graduate Somnath Sen. Sen wanted to do a movie and Singh decided to back him. The result is “Leela,” a film about cultural intricacies of the South Asian-American experience, that fuses Bollywood and Hollywood styles. “I didn’t know about the movie industry other than I had seen lots of movies,” he says.

“Now I know what it takes to do a movie from start to finish, and for my next project I want to produce my own by writing my own story and I want to direct it by myself.” Singh already has a synopsis ready and is studying screenwriting.

Show Business?

Singh sees a shift in Bollywood — with U.S. and European markets are being considered more intently as destinations for Indian films. He also sees the potential of doing Hollywood production in low-cost Bollywood, and is even working on a 3D animation project, where the animation will be done in India. As market forces align, it could be that Singh is onto a new market opportunity — just like in his startup days. But though Literate World is a business, Singh’s new foray into the world of media and film doesn’t seem to be driven by his acute business instincts and midas touch.His goals seem to be rather more artistic. “I like psychological treatments that bring out people’s personalities and the psychology behind why people do certain things,” he says when asked about his taste in films.

He lists his role models as Shyam Benegal, Mira Nair and Raj Kapoor — “on the show business side,” Sigh explains in reference to Kapoor.

“I’m a dreamer and so I can dream a lot of things and that’s what I enjoy,” he says. “High-tech is something I can revert to for earning a livelihood if I have to.”